DE3685829T2 - Heterocyclische amide. - Google Patents

Heterocyclische amide.

Info

Publication number: DE3685829T2
Authority: DE; Germany
Prior art keywords: thio; compound according; dimethylethyl; hydroxyphenyl; bis
Prior art date: 1985-02-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

DE8686101300T

Other languages

German (de)

English (en)

Other versions

DE3685829D1 (de

Inventor

Richard August Mueller

Richard Allen Partis

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

GD Searle LLC

Original Assignee

GD Searle LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-02-04

Filing date

1986-01-31

Publication date

1992-12-17

1986-01-31 Application filed by GD Searle LLC filed Critical GD Searle LLC

1992-08-06 Application granted granted Critical

1992-08-06 Publication of DE3685829D1 publication Critical patent/DE3685829D1/de

1992-12-17 Publication of DE3685829T2 publication Critical patent/DE3685829T2/de

2006-02-01 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims description 69
-1 heterocyclic amine Chemical group 0.000 claims description 25
206010020751 Hypersensitivity Diseases 0.000 claims description 21
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 21
206010061218 Inflammation Diseases 0.000 claims description 18
230000004054 inflammatory process Effects 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
208000006673 asthma Diseases 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
208000017520 skin disease Diseases 0.000 claims description 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
BOKNMZLKILLCNP-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-3-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(SCCC(=O)N2CCN(CC=3C=CC=CC=3)CC2)=C1 BOKNMZLKILLCNP-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
230000002062 proliferating effect Effects 0.000 claims description 3
OKXFKXBCHBVILH-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-3-(3,5-dichloro-4-hydroxyphenyl)sulfanylpropan-1-one Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1SCCC(=O)N1CCN(CC=2C=CC=CC=2)CC1 OKXFKXBCHBVILH-UHFFFAOYSA-N 0.000 claims description 2
RLCOVTUEXFVIDJ-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-3-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-1-one;hydrochloride Chemical compound Cl.CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(SCCC(=O)N2CCN(CC=3C=CC=CC=3)CC2)=C1 RLCOVTUEXFVIDJ-UHFFFAOYSA-N 0.000 claims description 2
FLNWYHTXYCFMSH-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-3-(4-hydroxy-3,5-diphenylphenyl)sulfanylpropan-1-one Chemical compound C1=C(C=2C=CC=CC=2)C(O)=C(C=2C=CC=CC=2)C=C1SCCC(=O)N(CC1)CCN1CC1=CC=CC=C1 FLNWYHTXYCFMSH-UHFFFAOYSA-N 0.000 claims description 2
ATOARTHPBMNKSD-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-1-pyrrolidin-1-ylbutan-1-one Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)CC(=O)N1CCCC1 ATOARTHPBMNKSD-UHFFFAOYSA-N 0.000 claims description 2
ABCPGDIVCJFHTI-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-1-pyrrolidin-1-ylpropan-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(SCCC(=O)N2CCCC2)=C1 ABCPGDIVCJFHTI-UHFFFAOYSA-N 0.000 claims description 2
AHKKWVXYCCZBKO-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-2-methyl-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1CCCN1C(=O)C(C)CSC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 AHKKWVXYCCZBKO-UHFFFAOYSA-N 0.000 claims description 2
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
WCQJZIZJUNRYOE-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-1-(4-methylpiperazin-1-yl)propan-1-one Chemical compound C1CN(C)CCN1C(=O)CCSC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WCQJZIZJUNRYOE-UHFFFAOYSA-N 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
239000000047 product Substances 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
239000000243 solution Substances 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
238000002360 preparation method Methods 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000002904 solvent Substances 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000000377 silicon dioxide Substances 0.000 description 17
239000007787 solid Substances 0.000 description 17
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 14
238000000034 method Methods 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 13
150000002617 leukotrienes Chemical class 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
NFVMNXZFSKGLDR-UHFFFAOYSA-N 2,6-ditert-butyl-4-sulfanylphenol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1O NFVMNXZFSKGLDR-UHFFFAOYSA-N 0.000 description 11
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 11
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 11
238000012360 testing method Methods 0.000 description 10
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 8
230000000172 allergic effect Effects 0.000 description 7
229940114079 arachidonic acid Drugs 0.000 description 7
235000021342 arachidonic acid Nutrition 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 6
201000004681 Psoriasis Diseases 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
206010003246 arthritis Diseases 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000010410 layer Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 5
208000010668 atopic eczema Diseases 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
230000037361 pathway Effects 0.000 description 5
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 4
KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 4
KGIJOOYOSFUGPC-XRXZHELTSA-N 5-hydroxyeicosatetraenoic acid Natural products CCCCCC=CCC=CCC=C\C=C\C(O)CCCC(O)=O KGIJOOYOSFUGPC-XRXZHELTSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 4
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 4
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000000770 proinflammatory effect Effects 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
YVNNRQCAABDUMX-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)prop-2-en-1-one Chemical compound CN1CCN(C(=O)C=C)CC1 YVNNRQCAABDUMX-UHFFFAOYSA-N 0.000 description 3
ZNHVWPKMFKADKW-LQWMCKPYSA-N 12(S)-HETE Chemical compound CCCCC\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=O ZNHVWPKMFKADKW-LQWMCKPYSA-N 0.000 description 3
LQBDPIUSHVJVQL-UHFFFAOYSA-N 2,6-dichloro-4-sulfanylphenol Chemical compound OC1=C(Cl)C=C(S)C=C1Cl LQBDPIUSHVJVQL-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
102000003820 Lipoxygenases Human genes 0.000 description 3
108090000128 Lipoxygenases Proteins 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229960001138 acetylsalicylic acid Drugs 0.000 description 3
239000002253 acid Substances 0.000 description 3
208000026935 allergic disease Diseases 0.000 description 3
230000007815 allergy Effects 0.000 description 3
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
229960005430 benoxaprofen Drugs 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
239000000575 pesticide Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
DTXYORKWCOQPMN-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) thiocyanate Chemical compound CC(C)(C)C1=CC(SC#N)=CC(C(C)(C)C)=C1O DTXYORKWCOQPMN-UHFFFAOYSA-N 0.000 description 2
ALDAIZWQFXPRRR-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)prop-2-en-1-one Chemical compound C1CN(C(=O)C=C)CCN1CC1=CC=CC=C1 ALDAIZWQFXPRRR-UHFFFAOYSA-N 0.000 description 2
MMSZAOIJVLACFN-UHFFFAOYSA-N 1-pyrrolidin-1-ylbut-2-en-1-one Chemical compound CC=CC(=O)N1CCCC1 MMSZAOIJVLACFN-UHFFFAOYSA-N 0.000 description 2
WLPAQAXAZQUXBG-UHFFFAOYSA-N 1-pyrrolidin-1-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCCC1 WLPAQAXAZQUXBG-UHFFFAOYSA-N 0.000 description 2
RVECLIMSIBKAOI-UHFFFAOYSA-N 2,6-diphenyl-4-sulfanylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=C(S)C=C1C1=CC=CC=C1 RVECLIMSIBKAOI-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
JSGBATMAAQLVPD-UHFFFAOYSA-N 4-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylbutanoic acid Chemical compound CC(C)(C)C1=CC(SCCCC(O)=O)=CC(C(C)(C)C)=C1O JSGBATMAAQLVPD-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
206010002198 Anaphylactic reaction Diseases 0.000 description 2
229940122204 Cyclooxygenase inhibitor Drugs 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
230000036783 anaphylactic response Effects 0.000 description 2
208000003455 anaphylaxis Diseases 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
210000003651 basophil Anatomy 0.000 description 2
238000004166 bioassay Methods 0.000 description 2
239000004044 bronchoconstricting agent Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
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239000012084 conversion product Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
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238000001035 drying Methods 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
210000003979 eosinophil Anatomy 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
YIGLRRLMAMUSIO-UHFFFAOYSA-N methyl 1-prop-2-enoylpyrrolidine-2-carboxylate Chemical compound COC(=O)C1CCCN1C(=O)C=C YIGLRRLMAMUSIO-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
230000008569 process Effects 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000012216 screening Methods 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
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208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
150000003595 thromboxanes Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
230000008728 vascular permeability Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
201000010653 vesiculitis Diseases 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/10—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)

DE8686101300T 1985-02-04 1986-01-31 Heterocyclische amide. Expired - Lifetime DE3685829T2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69804785A	1985-02-04	1985-02-04
US80996485A	1985-12-20	1985-12-20

Publications (2)

Publication Number	Publication Date
DE3685829D1 DE3685829D1 (de)	1992-08-06
DE3685829T2 true DE3685829T2 (de)	1992-12-17

Family

ID=27106139

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE8686101300T Expired - Lifetime DE3685829T2 (de)	1985-02-04	1986-01-31	Heterocyclische amide.

Country Status (5)

Country	Link
EP (1)	EP0190685B1 (fr)
JP (1)	JPH0733371B2 (fr)
AU (1)	AU584668B2 (fr)
CA (1)	CA1277663C (fr)
DE (1)	DE3685829T2 (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4959364A (en) *	1985-02-04	1990-09-25	G. D. Searle & Co.	Method of treating inflammation, allergy, asthma and proliferative skin disease using heterocyclic amides
DE3702755A1 (de) *	1987-01-30	1988-08-11	Hoechst Ag	3,5-di-tert.-butyl-4-hydroxybenzoesaeureamid, verschiedene von dessen derivaten, verfahren zur herstellung dieser verbindungen, die sie enthaltenden arzneimittel und ihre verwendung
IL85700A0 (en) *	1987-03-24	1988-08-31	Takeda Chemical Industries Ltd	1,4-disubstituted piperazine compounds,their production and use
US4835189A (en) *	1987-06-05	1989-05-30	G. D. Searle & Co.	Phenolic thioalkylamides as inhibitors of 5-lipoxygenase
JPS63310821A (ja) *	1987-06-05	1988-12-19	ジー．ディー．サール　アンド　カンパニー	５−リポキシゲナーゼの阻害剤としてのフエノール性チオエーテル、スルホキサイドおよびジスルフアイド
US5002967A (en) *	1987-06-05	1991-03-26	G. D. Searle & Co.	Phenolic thioethers, sulfoxides, and disulfides as inhibitors of 5-lipoxygenase
US5010080A (en) *	1988-12-02	1991-04-23	G. D. Searle & Co.	Use of heterocyclic amides to inhibit tumor metastasis
HU203872B (en) *	1989-07-14	1991-10-28	Richter Gedeon Vegyeszet	Process for producing amides of acrylic acid and their salts and pharmaceutical compositions containing them
IT1243364B (it) *	1990-07-26	1994-06-10	Zambon Spa	Processo di preparazione di intermedi utili per la sintesi del probucolo
PT98865A (pt) *	1990-09-07	1992-07-31	Searle & Co	Processo para a preparacao de tioeter-amidas fenolicas
US5082854A (en) *	1990-09-07	1992-01-21	G. D. Searle & Co.	Method of stimulating superoxide generation
US5189038A (en) *	1990-09-07	1993-02-23	G. D. Searle And Co.	Method of stimulating superoxide generation
AU690075B2 (en) *	1992-08-26	1998-04-23	Beiersdorf Aktiengesellschaft	Use of radical catchers as immunomodulating agents in cosmetic and dermatological compositions
DE4228455A1 (de) *	1992-08-26	1994-09-15	Beiersdorf Ag	Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Thiolen und/oder Thiolderivaten
US6207665B1 (en)	1997-06-12	2001-03-27	Schering Aktiengesellschaft	Piperazine derivatives and their use as anti-inflammatory agents
JP5227803B2 (ja)	2006-11-24	2013-07-03	ハイクスラボラトリーズ合同会社	スピロキノン化合物及び医薬組成物
CN101293880B (zh) *	2007-04-28	2010-11-03	中国石油天然气集团公司	一种制备n-丙烯酰吗啉的合成方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1936463A1 (de) *	1969-07-17	1971-02-04	Boehringer Sohn Ingelheim	Substituierte Phenole
US4029812A (en) *	1976-02-18	1977-06-14	The Dow Chemical Company	Novel hypolipidemic 2-(3,5-di-tert-butyl-4-hydroxyphenyl)thio carboxamides
AU518147B2 (en) *	1976-12-03	1981-09-17	E.R. Squibb & Sons, Inc.	Derivatives of thiazolidine, thiazine and morpholine carboxylic acids

1986
- 1986-01-31 EP EP86101300A patent/EP0190685B1/fr not_active Expired - Lifetime
- 1986-01-31 AU AU52885/86A patent/AU584668B2/en not_active Ceased
- 1986-01-31 DE DE8686101300T patent/DE3685829T2/de not_active Expired - Lifetime
- 1986-01-31 CA CA000500836A patent/CA1277663C/fr not_active Expired - Lifetime
- 1986-02-03 JP JP61021873A patent/JPH0733371B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU584668B2 (en)	1989-06-01
CA1277663C (fr)	1990-12-11
EP0190685B1 (fr)	1992-07-01
AU5288586A (en)	1986-08-07
EP0190685A3 (en)	1987-12-16
DE3685829D1 (de)	1992-08-06
EP0190685A2 (fr)	1986-08-13
JPH0733371B2 (ja)	1995-04-12
JPS61218570A (ja)	1986-09-29

Legal Events

Date	Code	Title	Description
1993-07-29	8364	No opposition during term of opposition
1997-01-16	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE3685829T2 (de)	1992-12-17	Heterocyclische amide.
DE3686168T2 (de)	1993-01-14	Hydroxyphenylthioalkylketoalkohole.
EP0190682B1 (fr)	1990-09-12	Hydroxy-4-phénylthioanilides disubstituées
EP0022958A1 (fr)	1981-01-28	Dérivés d'urée pour utilisation dans le traitement des troubles du métabolisme des matières grasses
DE3851232T2 (de)	1995-02-02	Substituierte chinoline.
US4981853A (en)	1991-01-01	Heterocyclic amides
DE10046029A1 (de)	2002-03-28	Indazole
DE3686729T2 (de)	1993-03-04	Aminoalkylpyridinamide.
DE3884858T2 (de)	1994-03-03	Phenol-thioalkylamide als Inhibitoren von 5-Lipoxygenase.
DE69014798T2 (de)	1995-04-27	Thionaphthalen-derivate, verfahren zur herstellung und antiallergisches mittel daraus.
DE3888394T2 (de)	1994-07-28	Phenolische Thioäther, Sulfoxide und Disulfide als Hemmstoffe der 5-Lipoxigenase.
EP0190684B1 (fr)	1990-07-25	Amides bicycloalkyl, tricycloalkyl, azabicycloalkyl et azatricycloalkyl
DE68910090T2 (de)	1994-03-10	Verwendung heterozyklischer Amide zur Verhinderung der Tumormetastasierung.
DE69107851T2 (de)	1995-08-03	Phenolische thioetheramide als 5-lipoxygenase-inhibitoren.
DE3883082T2 (de)	1993-12-16	Phenol-thioether als Inhibitoren von 5-Lipoxygenase.
DE68910282T2 (de)	1994-03-10	Acylaminoalkylpyridinamide als Inhibitoren der Tumormetastasierung.
EP0149818A2 (fr)	1985-07-31	Dérivés de 1,4-naphtoquinone, procédé pour leur préparation et leur utilisation comme médicaments
US5244899A (en)	1993-09-14	Azabicycloalkyl and azatricycloalkyl amides used to treat inflammation, allergy, asthma and skin disorders
US5157053A (en)	1992-10-20	Bicycloalky, tricycloalkyl, azabicycloalkyl, and azatricycloalkyl thio amides used to treat inflammation, allergy, asthma and skin disorders
US5019597A (en)	1991-05-28	Bicycloalkyl tricycloalkyl, azabicycloalkyl and azatricycoalkyl amides
EP0049538A2 (fr)	1982-04-14	Utilisation des dérivés de thiourée comme médicaments dans le traitement des dérèglements du métabolisme des lipides
US5225444A (en)	1993-07-06	Disubstituted 4-hydroxyphenylthio anilides
US5066679A (en)	1991-11-19	Phenolic thioalkylamides as inhibitors of 5-lipoxygenase
EP0227982A1 (fr)	1987-07-08	1-H-Pyrido[3,2-b][1,4]thiazines
US5198435A (en)	1993-03-30	Azabicycloalkyl and azatricycloalkyl amides